Cesium carbonate → Tert-Butyl Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}-acetate

Participants

Reaction Steps

8.16 g (23.1 mmol) of tert-butyl [4-(bromomethyl)phenyl](cyclopentyl)acetate, 3.7 g (21 mmol) of 2-phenyl-4H-1,3,4-oxadiazin-5(6H)-one and 7.53 g (23.1 mmol) of cesium carbonate in 147 ml of DMF were stirred at room temperature for 12 h. The reaction solution was then stirred with saturated aqueous sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and evaporated to dryness under reduced pressure. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 5:1). This gave 6.51 g (14.5 mmol, 69% of theory) of the title compound.

Provenance & Evidence